YAZOO CITY, Miss. — For the past five months, U.S. Senate candidate Mike Espy has tried to remind Mississippians how he has served them in the past: a son of the Delta with three terms in the U.S. House who spent time as Bill Clinton’s agriculture secretary.

But even Espy’s most ardent supporters worry that when many voters go to the polls on Nov. 6, what Espy has done will matter much less than what he is: a black man running for one of the highest elected offices in a state with a Confederate emblem on its flag.

One of his opponents is hearkening to another version of the past: Republican Chris McDaniel, a conservative fond of provocative statements whose yard signs boast the “stainless banner” — the second flag of the Confederate States of America.

The state’s appointed Sen. Cindy Hyde-Smith, a Republican, is the other candidate who will be on the special-election ballot; she took over from Thad Cochran, who resigned in ill health in April. The winner will fill the remaining two years of Cochran’s term; if no candidate wins a majority, the race heads to a Nov. 27 runoff.

Espy, 64, whose family has deep roots in Mississippi, must draw large numbers of black and Democratic voters to the polls. But his biggest challenge will be persuading a large enough swath of others, including white moderates, to ignore the two main Republicans on the ballot and vote for a Democrat who happens to be black.

“Mississippi politics is black and white,” said Joe Thomas Jr., the Democratic county chair from Yazoo County, which includes Espy’s hometown, Yazoo City.

Former congressman Mike Espy, a Democratic candidate in a special election to fill the final two years of a term started by Republican U.S. Sen. Thad Cochran of Mississippi, speaks at the Neshoba County Fair in Philadelphia, Miss., earlier this year. (Rogelio V. Solis/AP)

“Nobody will come out and say that, but everybody knows it,” said Thomas, who is African American. “We’re 50 years removed from the civil rights movement, but it’s still Mississippi.”

Espy is one of three prominent African American candidates running for statewide offices in the South in November. Andrew Gillum of Florida and Stacey Abrams of Georgia won Democratic nominations for governor and are seeking to become the first African American chief executives of their respective states.

Their candidacies build on nationwide successes in 2017, such as the election of Justin Fairfax, the African American Democrat who in January was sworn in as lieutenant governor in Virginia — a few steps from where Gen. Robert E. Lee accepted command of Confederate troops.

But the South has not suddenly morphed into a post-racial utopia. Some politicians and their supporters have used rhetoric about Confederate statues and symbols, the not-so-distant memory of a white supremacist march in Charlottesville last year and loaded language to stir up deep-seated divisions and mobilize specific voters.

Within hours of Gillum’s primary victory in Florida, his Republican opponent, former Rep. Ron DeSantis, told reporters that voters couldn’t afford to “monkey this up” by electing Gillum. A few days later, some Florida voters heard a jungle-music-infused robo-call insulting African Americans over background sounds of drums and monkeys. Gillum has accused his opponents of trying to “weaponize race.”

In Mississippi, where Espy is seeking to become the first black senator from the state since shortly after the Civil War, the difficulty facing him is underscored by the unbroken line of white, male faces that have led the state for the past century and a half. And it is exemplified by McDaniel’s tactics.

McDaniel is an ardent supporter of the Confederate flag and recently polled his Twitter followers on whether “in light of all the political correctness and leftist hysteria,” history should consider Robert E. Lee a hero or a villain. (The final tally: 91 percent said villain; 9 percent said hero.)

During a September appearance on MSNBC’s “Morning Joe,” McDaniel was asked what he would say to black voters who are skeptical of him.

“I’m going to ask them after 100 years, after 100 years of relying on big government to save you, where are you today?” McDaniel said. “After 100 years of begging for federal government scraps, where are you today?” The comment drew boos from the live crowd at Ole Miss.

McDaniel told a mostly white group of supporters gathered at a community center in Pearl, Miss., the accusations that he was making his campaign about race were an effort by his opponents to thwart him.

“If you noticed, I do not have horns on my head. There’s no tail or pitchfork,” he said. “If you watch the attack ads, that’s what they’re going to talk about, all these side issues, the smear campaign, and here’s why: They can’t defend their record.”

His town hall meeting erupted in applause when he said Hillary Clinton deserved to be “in a federal penitentiary” and that illegal immigration was one of the nation’s top national security issues.

McDaniel defended his support of the Confederate flag and statues and noted that Mississippians affirmed keeping the Confederate symbol on the state’s flag in a 2001 referendum. He said he thinks Espy is a fine person, but Mississippi won’t send “a liberal Democrat to the U.S. Senate.”

The demography of Mississippi requires that Espy play down the role of race. Blacks make up roughly 38 percent of the population, the largest percentage of all the former Confederate states, but nowhere near a majority.

Espy noted that in his other bids for office, he has won substantial support from white voters. Forty percent of them supported him in his last congressional bid, in 1992, up from 12 percent in his first bid for Congress, exit polls showed.

“The path to victory runs through the black community,” Espy said. “We have to get a very large African American turnout on November 6th. If we don’t get it, I’m going to lose. If we get it, I can win. But I can’t win alone with black votes. It’s not possible.”

For Espy, going after white moderates is occasionally a matter of linguistic gymnastics. Instead of talking about the Affordable Care Act, for example, Espy focuses on rural hospitals that have had to close because state leaders won’t accept Medicaid funds — an expansion offered by the ACA, also known as Obamacare.

He reminds voters of the time he endorsed Republican Haley Barbour for governor — a sign, he says, he will work with anyone who has ideas that are good for Mississippi.

The need for careful navigation was learned in childhood. Espy’s grandfather, Thomas Jefferson Huddlesworth, made his fortune running dozens of funeral and nursing homes across Mississippi. He started the Afro American Sons and Daughters fraternal organization, which operated the first black hospital in Mississippi. Nearly a century later, Huddlesworth is still remembered as the first black man in the Delta to own a Cadillac.

He also started a newspaper for blacks, which he used to invoke the importance of getting an education and a job or joining a social club. But he shied away from some of the most incendiary issues of the Jim Crow era and the civil rights movement, Espy said, “because he’d be lynched the next day.”

In his most visible sign of calibration, Espy has declined to go on offense against President Trump, as other Democrats have, for fear of alienating potential crossover voters. Instead, he has emphasized that he is a conservative Democrat who will work with anyone.

But even that strategy is risky, said Marvin King, a political scientist at the University of Mississippi who specializes in racial and ethnic politics.

“The Republican Party has been very successful at making the conservative Democrat extinct,” King said. “They’ve been redistricted, gerrymandered out of existence. If someone wants to vote for a conservative in Mississippi, they’re going to vote for a Republican.”

In painting himself as a bridge builder, King said, “Espy is holding out hope for a model that doesn’t exist anymore. What he’s doing is what Democrats here have done in the past. If that’s your strategy, then you’re going to lose.”

Also problematic is Espy’s association with the Clintons. A few weeks into his fourth congressional term, Espy was confirmed as President Bill Clinton’s agriculture secretary. He resigned a year later amid allegations that he had received improper gifts. Shortly afterward, he was indicted, although ultimately acquitted.

Hyde-Smith, who has been endorsed by Trump, said that negative incident is enduring for Mississippi voters.

“The way that he left office, people remember that more than they remember how he was in office,” she said.

That sentiment was echoed by people who attended McDaniel’s town hall meeting. Marc Allen, a 62-year-old Air Force veteran from Pearl, said he was leaning toward McDaniel because he didn’t trust Hyde-Smith’s conservative bona fides. He said he had not done much research on Espy but did not like that Espy had been a Clinton appointee.

“I can’t say I know much about him,” said Allen, who is white. “But I do know who he has aligned himself with. I just could not see myself voting for him.”

Ferrel Guillory, director of the Program on Public Life at the University of North Carolina, said Espy is “the kind of black candidate who would have a relatively strong appeal to white voters . . . while energizing a stronger turnout among black voters.”

That means opponents must mobilize the state’s most conservative voters, using “dog whistles or little rhetorical flourishes that try to offset the potential for black turnout with an increase in white turnout,” Guillory said.

Cristen Hemmins, an Espy supporter who is white, said he has something other statewide Democratic candidates have lacked: name recognition.

Espy’s bid, Hemmins said, “definitely feels like a one-in-a-million opportunity for us to get out the Democratic vote.”

Espy said he hopes his election could change the state’s view of itself. Mississippi consistently ranks below almost every other state in measures of socioeconomic success, including obesity rates and educational attainment.

“We are a state in need of uplift in a ubiquitous way,” he said. “A state like Mississippi that is moving toward the second decade of the 21st century has to be a state that the world sees as moving forward, and symbols are a good part of that, so I’ll be sort of a globalized symbol for new Mississippi.”